Bis(2,4-dichloro­phen­oxy­acetato-κ2 O 1,O 1′)(5,5′-dimethyl-2,2′-bipyridine-κ2 N,N′)cobalt(II)

Li-Li Ji; Jian-She Liu; Wen-Dong Song

doi:10.1107/S1600536811010579

. 2011 Mar 26;67(Pt 4):m493. doi: 10.1107/S1600536811010579

Bis(2,4-dichlorophenoxyacetato-κ² O ¹,O ^1′)(5,5′-dimethyl-2,2′-bipyridine-κ² N,N′)cobalt(II)

Li-Li Ji ^a, Jian-She Liu ^a,^*, Wen-Dong Song ^b

PMCID: PMC3099758 PMID: 21754003

Abstract

In the title compound, [Co(C₈H₅Cl₂O₃)(C₁₂H₁₂N₂)], the Co^II atom, lying on a twofold rotation axis, is coordinated by four O atoms from two chelating 2,4-dichlorophenoxyacetate ligands and two N atoms from a 5,5′-dimethyl-2,2′-bipyridine ligand, displaying a distorted octahedral geometry. A three-dimensional supramolecular structure is formed through intermolecular C—H⋯O hydrogen bonds and π–π stacking interactions between the pyridine and benzene rings [centroid–centroid distance = 3.779 (2) Å].

Related literature

For related structures with 2,4-dichlorophenoxyacetate ligands, see: Liu (2010 ▶); Song & Xi (2006 ▶).

Experimental

Crystal data

[Co(C₈H₅Cl₂O₃)(C₁₂H₁₂N₂)]
M _r = 683.21
Monoclinic,
a = 13.397 (2) Å
b = 8.4152 (14) Å
c = 13.752 (2) Å
β = 112.570 (3)°
V = 1431.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.756, T _max = 0.819
10343 measured reflections
2567 independent reflections
2229 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.106
S = 1.14
2567 reflections
187 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010579/hy2417sup1.cif

e-67-0m493-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010579/hy2417Isup2.hkl

e-67-0m493-Isup2.hkl^{(126.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O3ⁱ	0.97	2.49	3.391 (3)	154
C12—H12⋯O2ⁱⁱ	0.93	2.40	3.157 (4)	139

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge Donghua University for supporting this work.

supplementary crystallographic information

Comment

In the structural investigation of 2,4-dichlorophenoxyacetate complexes, it has been found that 2,4-dichlorophenoxyacetic acid functions as a multidentate ligand (Liu, 2010; Song & Xi, 2006), with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, a new Co(II) complex obtained by the reaction of 2,4-dichlorophenoxyacetic acid, 5,5'-dimethyl-2,2'-bipyridine and cobalt nitrate hexahydrate in an alkaline aqueous solution.

As illustrated in Fig. 1, the Co^II atom, lying on a twofold rotation axis, exists in an distorted octahedral environment defined by four carboxylate O atoms from two different bidentate 2,4-dichlorophenoxyacetate ligands and two N atoms from one 5,5'-dimethyl-2,2'-bipyridine ligand. Intermolecular C—H···O hydrogen bonds (Table 1) and π–π stacking interactions are observed (Fig. 2). The centroid–centroid distance between a pyridine ring and a benzene ring at (1-x, 1-y, -z) is 3.779 (2) Å, thus indicating a weak π–π stacking interaction.

Experimental

A mixture of 2,4-dichlorophenoxyacetic acid (0.110 g, 0.5 mmol), 5,5'-dimethyl-2,2'-bipyridine (0.092 g, 0.5 mmol), cobalt nitrate hexahydrate (0.145 g, 0.5 mmol), NaOH (0.08 g, 0.2 mmol) and H₂O (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 423 K for 3 days, and then cooled to room temperature at a rate of 10 K h^-1. The block purple crystals obtained were washed with water and dried in air (yield: 45% based on Co).